Substituted iminoalkoxy-phenyluracils, the production and use thereof as herbicides

Abstract

The invention relates to novel substituted iminoalkoxy-phenyluracils of the general formula (I) in which R 1 is hydrogen, amino or optionally substituted alkyl, R 2 is carboxyl, cyano, carbamoyl, thiocarbamoyl or alkyl or alkoxycarbonyl, the latter two being optionally substituted, R 3 is hydrogen, halogen or optionally substituted alkyl, R 4 is hydrogen, cyano, thiocarbamoyl or halogen, R 5 is cyano, thiocarbamoyl or halogen, R 6 is hydrogen or optionally substituted alkyl, R 7 is optionally substituted alkyl, and R 8 is hydroxyl, amino or a radical of the series alkyl, alkoxy, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino, alkylsulfonylamino, alkenyl, alkynyl, alkenyloxy, alkynyloxy, aryl, aryloxy, arylamino, arylcarbonylamino, arylsufonylamino, arylalkyl, arylalkylamino, arylalkylcarbonylamino or arylalkylsulfonylamino, each of which is optionally substituted. The invention further relates to methods for producing said compounds and their use as herbicides.

What is claimed is:  
     
       1. A substituted iminoalkoxy-phenyluracil of the general formula (I),                    
       wherein 
       R 1  represents hydrogen, amino, C 1 -C 8  alkyl, or cyano-, fluorine-, chlorine- or C 1 -C 4 -alkoxy-substituted C 1 -C 6 -alkyl,  
       R 2  represents carboxyl, cyano, carbamoyl, thiocarbamoyl, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, or represents in each case cyano-, fluorine-, chlorine- or C 1 -C 4 -alkoxy-substituted C 1 -C 4 -alkyl or C 1 -C 4 -alkoxycarbonyl,  
       R 3  represents hydrogen, halogen, C 1 -C 4 -alkyl, or flourine- or chlorine-substituted C 1 -C 4 -alkyl,  
       R 4  represents hydrogen, cyano, thiocarbamoyl or halogen,  
       R 5  represents cyano, thiocarbamoyl or halogen,  
       R 6  represents hydrogen, C 1 -C 6 -alkyl, or cyano-, fluorine-, chlorine- or C 1 -C 4 -alkoxyl-substituted C 1 -C 6 -alkyl,  
       R 7  represents C 1 -C 6  alkyl, or cyano-, fluorine, chlorine- or C 1 -C 1 -alkoxy-substituted C 1 -C 6 -alkyl, and  
       R 8  represents hydroxyl; amino; a radical selected from the group consisting of C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylamino, di(C 1 -C 6 )-alkylamino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkylsulphonylamino, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 6 -C 10 -aryl, C 6 -C 10 -aryloxy, C 6 -C 10 -arylamino, C 6 -C 10 -arylcarbonylamino, C 6 -C 10 -arylsuphonylamino, C 6 -C 10 -aryl-C 1 -C 4 -alkyl, C 6 -C 10 -aryl-C 1 -C 4 -alkylamino, C 6 -C 10 -aryl-C 1 -C 4 -alkylcarbonylamino and C 6 -C 10 -aryl-C 1 -C 4 -alkylsulphonylamino; a radical selected from the group consisting of carboxyl-, cyano-, halogen-, C 1 -C 4 -alkoxy- or C 1 -C 4 -allkoxy-carbonyl-substituted C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylamino, di(C 1 -C 6 )-alkylamino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino and C 1 -C 6 -alkylsulphonylamino; a radical selected from the group consisting of halogen-substituted C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 -alkenyloxy and C 3 -C 6 -alkynyloxy; or a radical selected from the aroup consisting of nitro-, cyano-, carboxyl-, halogen-, C 1 -C 4 -alkyl-, C 1 -C 4 -halogenoalkyl-, C 1 -C 4 -alkoxy- or C 1 -C 4 -halogenalkoxy-substituted C 6 -C 10 -aryl, C 6 -C 10 -aryloxy, C 6 -C 10 -arylamino, C 6 -C 10 -arylcarbonylamino, C 6 -C 10 -arylsulphonylamino, C 6 -C 10 -aryl-C 1 -C 4 -alkyl, C 6 -C 10 -aryl-C 1 -C 4 -alkylamino, C 6 -C 10 -aryl-C 1 -C 4 -alkylcarbonylamino and C 6 -C 10 -aryl-C 1 -C 4 -alkylsulphonylamino.  
     
     
       2. A process for preparing a substituted iminoalkoxy-phenyluracil of the general formula (I)                    
       wherein 
       R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7  and R 8  are as defined in claim  1 ,  
       comprising the step of reacting a substituted oxoalkoxy-phenyluracil of the general formula (II)                    
       wherein 
       R 1 , R 2 , R 3 , R 4 , R 5 , R 6  and R 7  are as defined above  
       with an amino compound of the general formula (III) 
       
         
           H 2 N—R 8   (III)  
         
       
       wherein 
       R 8  is as defined above  
       or with an acid adduct of the compound of the general formula (III). 
     
     
       3. A herbicidal composition, comprising at least one substituted iminoalkoxy-phenyluracil of the formula (I) according to claim  1  and one or more extenders and/or surfactants. 
     
     
       4. A method for controlling undesirable plants, comprising the step of allowing a herbicidally effective amount of a substituted iminoalkoxy-phenyluracil of the formula (I) according to claim  1  to act on at least one of undesirable plants and their habitat.